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Atropselective Organocatalytic Synthesis of Chiral Compounds Containing Nitrogen along the Axis of Chirality

Ana Maria Faísca Phillips, Armando J. L. Pombeiro

2023Symmetry10 citationsDOIOpen Access PDF

Abstract

Atropisomers, i.e., stereoisomers that are distinct because their free rotation about a single bond is hindered by steric interactions between nearby bulky groups or by electrostatics, may interact with their surroundings in different ways, and may also exhibit different properties. They may be found as natural products, as pharmaceutical or agricultural active ingredients, as chiral ligands and organocatalysts, and in functional materials. Our ability to synthesize them stereoselectively and in a sustainable way, using achiral materials and simply with the aid of an organocatalyst and mild conditions, has become a hot topic in research. This review provides an overview of recent achievements in the synthesis of atropisomers containing C-N and N-N axes of chirality.

Topics & Concepts

AtropisomerChirality (physics)Steric effectsAxial chiralityOrganocatalysisChemistryStereochemistryEnantioselective synthesisOrganic chemistryCatalysisPhysicsChiral symmetry breakingNambu–Jona-Lasinio modelQuantum mechanicsQuarkAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAsymmetric Synthesis and Catalysis
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